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The Best Sean Penn Movies

Updated November 13, 2019 3.0k votes 524 voters 40.2k views55 items

List RulesVote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Sean Penn movies, ranked best to worst with movie trailers when available. Sean Penn's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Sean Penn movies is decided by how many votes they receive, so only highly rated Sean Penn movies will be at the top of the list. Sean Penn has been in a lot of films, so people often debate each other over what the greatest Sean Penn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Sean Penn films to end the squabble once and for all.

If you think the best Sean Penn role isn't at the top, then upvote it so it has the chance to become number one. The greatest Sean Penn performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

List films include Up at the Villa, This So-Called Disaster and many more.

"This list answers the questions, "What are the best Sean Penn movies?" and "What are the greatest Sean Penn roles of all time?"

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  • Mystic River1
    107
    34

    Mystic River

    Emmy Rossum, Sean Penn

    Released2003

    Directed byClint Eastwood

    Mystic River is a 2003 American mystery drama film directed and scored by Clint Eastwood. It... more on Wikipedia
  • The Weight of Water2
    76
    12

    The Weight of Water

    Elizabeth Hurley, Sean Penn

    Released2000

    Directed byKathryn Bigelow

    The Weight of Water is a 2000 French-American mystery thriller film based on Anita Shreve's... more on Wikipedia
  • The Interpreter3
    72
    16

    The Interpreter

    Nicole Kidman, Sean Penn

    Released2005

    Directed bySydney Pollack

    The Interpreter is a 2005 political thriller film starring Nicole Kidman, Sean Penn, and... more on Wikipedia
  • Dead Man Walking4
    88
    33

    Dead Man Walking

    Sean Penn, Susan Sarandon

    Released1995

    Directed byTim Robbins

    This film is a 1995 American drama film starring Susan Sarandon and Sean Penn, and co-produced... more on Wikipedia

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  • Fast Times at Ridgemont High5
    96
    40

    Fast Times at Ridgemont High

    Nicolas Cage, Sean Penn

    Released1982

    Directed byAmy Heckerling

    Fast Times at Ridgemont High is a 1982 American coming-of-age teen comedy film written by... more on Wikipedia

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  • Carlito's Way6
    84
    31

    Carlito's Way

    Al Pacino, Sean Penn

    Released1993

    Directed byBrian De Palma

    Carlito's Way is a 1993 American drama film directed by Brian De Palma, based on the novels... more on Wikipedia

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  • The Game7
    64
    22

    The Game

    Sean Penn, Michael Douglas

    Released1997

    Directed byDavid Fincher, Pedro Coutinho

    The Game is a 1997 American mystery thriller film directed by David Fincher, starring Michael... more on Wikipedia

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  • Bad Boys8
    74
    35

    Bad Boys

    Sean Penn, Ally Sheedy

    Released1983

    Directed byRick Rosenthal

    Bad Boys is a 1983 drama film written by Richard Di Lello and directed by Rick Rosenthal.

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  • Up at the Villa9
    43
    10

    Up at the Villa

    Sean Penn, Anne Bancroft

    Released2000

    Directed byPhilip Haas

    Up at the Villa is a 2000 drama film written by W. Somerset Maugham and directed by Philip...Amazon_watch buy button
  • All the King's Men10
    47
    14

    All the King's Men

    Kate Winslet, Sean Penn

    Released2006

    Directed bySteven Zaillian

    All the King's Men is a 2006 film adaptation of the 1946 Pulitzer Prize-winning novel All the... more on Wikipedia
  • I Am Sam11
    76
    43

    I Am Sam

    Sean Penn, Dakota Fanning

    Released2001

    Directed byJessie Nelson

    I Am Sam is a 2001 American drama film directed by Jessie Nelson. A mentally handicapped man... more on Wikipedia

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  • Milk12
    67
    35

    Milk

    James Franco, Sean Penn

    Released2008

    Directed byGus Van Sant

    Milk is a 2008 American biographical film based on the life of gay rights activist and... more on Wikipedia

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  • Hurlyburly13
    56
    27

    Hurlyburly

    Meg Ryan, Anna Paquin

    Released1998

    Directed byAnthony Drazan

    Hurlyburly is a 1998 independent film, based on the acclaimed 1984 play of the same name by... more on Wikipedia
  • 21 Grams14
    50
    22

    21 Grams

    Naomi Watts, Sean Penn

    Released2003

    Directed byAlejandro González Iñárritu

    21 Grams is a 2003 American drama film directed by Mexican director Alejandro González... more on Wikipedia

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  • Colors15
    52
    24

    Colors

    Sean Penn, Robert Duvall

    Released1988

    Directed byDennis Hopper

    Colors is a 1988 American police procedural action film starring Sean Penn and Robert Duvall,... more on Wikipedia

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  • At Close Range16
    49
    22

    At Close Range

    Sean Penn, Christopher Walken

    Released1986

    Directed byJames Foley

    At Close Range is a 1986 crime drama film directed by James Foley, based on the real life... more on Wikipedia
  • Before Night Falls17
    29
    15

    Before Night Falls

    Johnny Depp, Sean Penn

    Released2000

    Directed byJulian Schnabel

    Before Night Falls is a 2000 American drama film directed by Julian Schnabel. The screenplay... more on Wikipedia

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  • Taps18
    26
    14

    Taps

    Tom Cruise, Sean Penn

    Released1981

    Directed byHarold Becker

    Taps is a 1981 drama film starring George C. Scott and Timothy Hutton, with Ronny Cox, Tom... more on Wikipedia

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  • Judgment in Berlin19
    20
    9

    Judgment in Berlin

    Sean Penn, Martin Sheen

    Released1988

    Directed byLeo Penn

    Judgment in Berlin is a 1988 drama film written by Herbert J. Stern, Joshua Sinclair and Leo...Amazon_watch buy button
  • Fair Game20
    36
    31

    Fair Game

    Naomi Watts, Sean Penn

    Released2010

    Directed byDoug Liman

    Fair Game is a 2010 biographical spy drama film directed by Doug Liman and starring Naomi... more on Wikipedia

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  • Crackers21
    17
    13

    Crackers

    Sean Penn, Donald Sutherland

    Released1984

    Directed byLouis Malle

    Crackers is a 1984 American film directed by Louis Malle. It was entered into the 34th Berlin... more on Wikipedia
  • The Cutting Edge: The Magic of Movie Editing22
    14
    9

    The Cutting Edge: The Magic of Movie Editing

    Jodie Foster, Steven Spielberg

    Released2004

    Directed byWendy Apple

    The Cutting Edge: The Magic of Movie Editing is a 2004 documentary film directed by filmmaker... more on Wikipedia
  • What Just Happened23
    23
    22

    What Just Happened

    Kristen Stewart, Bruce Willis

    Released2008

    Directed byBarry Levinson

    What Just Happened is a satirical comedy-drama directed by Barry Levinson and starring Robert... more on Wikipedia
  • Racing with the Moon24
    23
    22

    Racing with the Moon

    Nicolas Cage, Sean Penn

    Released1984

    Directed byRichard Benjamin

    Racing with the Moon is a 1984 American drama film starring Sean Penn, Elizabeth McGovern, and... more on Wikipedia

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  • It's All About Love25
    19
    18

    It's All About Love

    Sean Penn, Claire Danes

    Released2003

    Directed byThomas Vinterberg

    It's All About Love is a 2003 romance-drama film written and directed by Thomas Vinterberg.... more on Wikipedia

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